intermediates
5.6.4.1 (R,E)-1-(1,3-Dioxoisoindolin-2-yl)dodec-2-en-5-yl (R)-3,3,3-trifluoro-2- methoxy-2-phenylpropanoate (96)
To a solution of (R,E)-2-(5-hydroxydodec-2-en-1-yl)isoindoline-1,3-dione 95 (20.0 mg, 60.7 µmol, 1.0 eq.) in DCM (600 µL) was added a solution of (R)-(+)-α-methoxy-α- trifluoromethylphenylacetic acid (MTPA) (15.6 mg, 66.8 µmol, 1.1 eq.) in DCM (200 µL), followed by EDC (12.8 mg, 66.8 µmol, 1.1 eq.) and DMAP (820 µg, 6.07 µmol, 0.1 eq.). The reaction was stirred at room temperature for 16 h, at which time 2 M HCl
(1 mL) and H2O (10 mL) were added. The layers were separated and the aqueous extracted with DCM (2 × 10 mL). The combined organics were dried over anhydrous MgSO4, concentrated under reduced pressure and the crude residue purified by silica gel chromatography (1 : 3 EtOAc : pet. ether) to afford (R,R)-96 as a colourless oil (18.0 mg, 54 %). δH (CDCl3, 500 MHz): 0.86 (t, 3H, H-24, J = 7.0 Hz), 1.07-1.31 (m, 10H, H-19–23), 1.47-1.60 (m, 2H, H-18), 2.37 (t, 2H, H-8, J = 6.0 Hz), 3.51 (s, 3H, H-13), 4.23 (d, 2H, H-5, J = 5.5 Hz), 5.09 (quint, 1H, H-9, J = 6.0 Hz), 5.61 (dt, 1H, H-6, J = 15.5 Hz, 6.0 Hz), 5.67 (dt, 1H, H-7, J = 15.5 Hz, 6.5 Hz), 7.37-7.41 (m, 3H, H-15, H-17), 7.49-7.54 (m, 2H, H-16), 7.71 (dd, 2H, H-1, J = 5.5 Hz, 3.0 Hz), 7.84 (dd, 2H, H-2, J = 5.5 Hz, 3.0 Hz); δC (CDCl3, 125 MHz): 14.2 (C-24), 22.7 (C-23), 24.9 (C-21), 29.2 (C-20), 29.3 (C-19), 31.8 (C-22), 33.3 (C-18), 36.8 (C-8), 39.4 (C-5), 55.6 (C-13), 76.5 (C-9), 84.7 (C-11), 123.4 (C-2), 124.6 (C-12), 127.3 (C-6), 127.4 (C-16), 128.5 (C-15), 129.2 (C-17), 129.7 (C-7), 132.3 (C-14), 132.5 (C-3), 134.1 (C-1), 166.3 (C-10), 168.0 (C-4); HRMS: Calculated for [M+Na]+ 568.2281, found 568.2286.
153
5.6.4.2 (R,E)-1-(1,3-Dioxoisoindolin-2-yl)dodec-2-en-5-yl (S)-3,3,3-trifluoro-2- methoxy-2-phenylpropanoate (96)
Compound (R,S)-96 was synthesised from (R)-95 and (S)-(−)-MTPA, following the procedure described for the synthesis of (R,R)-96. Yield: 16.8 mg, 51 %.
δH (CDCl3, 500 MHz): 0.87 (t, 3H, H-24, J = 7.0 Hz), 1.16-1.35 (m, 10H, H-19–23), 1.50-1.66 (m, 2H, H-18), 2.31 (t, 2H, H-8, J = 6.0 Hz), 3.51 (s, 3H, H-13), 4.16 (d, 2H, H-5, J = 5.0 Hz), 5.09 (quint, 1H, H-9, J = 6.0 Hz), 5.50 (dt, 1H, H-6, J = 15.5 Hz, 5.5 Hz), 5.57 (dt, 1H, H-7, J = 15.5 Hz, 6.5 Hz), 7.30-7.34 (m, 3H, H-15, H-17), 7.42-7.46 (m, 2H, H-16), 7.64 (m, 2H, H-1, J = 5.5 Hz, 3.0 Hz), 7.77 (dd, 2H, H-2, J = 5.5 Hz, 3.0 Hz); δC (CDCl3, 125 MHz): 14.2 (C-24), 22.7 (C-23), 25.3 (C-21), 29.2 (C-20), 29.4 (C-19), 31.8 (C-22), 33.3 (C-18), 36.4 (C-8), 39.4 (C-5), 55.6 (C-13), 76.6 (C-9), 84.7 (C-11), 123.4 (C-2), 127.2 (C-6), 127.5 (C-16), 128.5 (C-15), 128.9 (C-17), 129.7 (C-7), 132.3 (C-14), 132.5 (C-3), 134.1 (C-1), 166.3 (C-10), 168.0 (C-4); HRMS: Calculated for [M+Na]+ 568.2281, found 568.2286. 5.6.4.3 (S,E)-1-(1,3-Dioxoisoindolin-2-yl)dodec-2-en-5-yl (R)-3,3,3-trifluoro-2- methoxy-2-phenylpropanoate (96)
154
Compound (S,R)-96 was synthesised from (S)-95 and (R)-(+)-MTPA, following the procedure described for the synthesis of (R,R)-96. Yield: 21.4 mg, 65 %. NMR and LRMS data are consistent with those for (R,S)-96.
5.6.4.4 (S,E)-1-(1,3-Dioxoisoindolin-2-yl)dodec-2-en-5-yl (S)-3,3,3-trifluoro-2- methoxy-2-phenylpropanoate (96)
Compound (S,S)-96 was synthesised from (S)-95 and (S)-(−)-MTPA, following the procedure described for the synthesis of (R,R)-96. Yield: 20.5 mg, 62 %. NMR and LRMS data are consistent with those for (R,R)-96.
5.6.5
Synthesis of CpkD substrate
5.6.5.1 Ethyl (2E,4E,6E)-octa-2,4,6-trienoate (99)
To a stirred suspension of NaH (75.2 mg, 3.13 mmol, 1.2 eq.) in anhydrous THF (5 mL) at 0 °C under argon was added triethyl-4-phosphonoacetate (621 µL, 3.13 mmol, 1.2 eq.), dropwise. The mixture was stirred for 1 h, at which time a solution of trans,trans-2,4- hexadienal 100 (288 µL, 2.61 mmol, 1 eq.) in THF (2.5 mL) was added dropwise. The reaction was allowed to warm to room temperature and stirred until completion. The reaction was then quenched with sat. aq. NH4Cl (10 mL) and the aqueous phase extracted with Et2O (3 × 15 mL). The combined organics were washed with H2O (10 mL), brine (10 mL) and dried over anhydrous MgSO4. The solvent was removed under reduced
155
pressure and the crude residue purified by silica gel chromatography (1 : 9 EtOAc : pet. ether) to afford 99 as a white solid (312 mg, 72 %).
Note: compound exists as mixture of geometric isomers (E:Z ≈ 9:1) and m.p. not obtained due to polymerisation; δH (CDCl3, 300 MHz): 1.21 (t, 3H, H-1, J = 7.0 Hz), 1.75 (d, 3H, H-10, J = 7.0 Hz), 4.12 (q, 2H, H-2, J = 7.0 Hz), 5.76 (d, 1H, H-4, J = 15.5 Hz), 5.77-5.91 (m, 1H, H-9), 6.00-6.16 (m, 2H, H-6, H-8), 6.45 (dd, 1H, H-7, J = 15.0 Hz, 10.5 Hz), 7.22 (dd, 1H, H-5, J = 15.5 Hz, 11.5 Hz); δC (CDCl3, 75 MHz): 14.4 (C-1), 16.6 (C-10), 60.3 (C-2), 120.2 (C-4), 127.7 (C-8), 131.3 (C-6), 135.1 (C-7), 141.1 (C-8), 144.9 (C-5), 167.3 (C-3); HRMS: Calculated for [M+Na]+ 189.0886; found 189.0888. Data are consistent with those reported by Goodreid and coworkers.223
156
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